1-Boc-2,5-Dihydro-1H-pyrrole-3-boronic acid, pinacol ester Chemical Properties

Boiling point:

330.5±52.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

-1.18±0.40(Predicted)

form 

solid

color 

Off-white to light yellow

InChI

InChI=1S/C15H26BNO4/c1-13(2,3)19-12(18)17-9-8-11(10-17)16-20-14(4,5)15(6,7)21-16/h8H,9-10H2,1-7H3

InChIKey

OIZXJJIHVIYNKZ-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC=C(B2OC(C)(C)C(C)(C)O2)C1

Safety Information

HS Code 

2933998090

1-Boc-2,5-Dihydro-1H-pyrrole-3-boronic acid, pinacol ester Usage And Synthesis

Uses

1-Boc-2,5-Dihydro-1H-pyrrole-3-boronic acid, pinacol ester can be used in the synthesis of series of kinase inhibitors.

Synthesis

General procedure for the synthesis of tert-butyl 1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-3-boronic acid pinacol ester from tert-butyl 3-(trifluoromethanesulfonyloxy)-2H-pyrrole-1(5H)-carboxylate and pinacol ester of bis(boronic acid): tert-butyl 3-(trifluoromethanesulfonyloxy)-2,5-dihydro-pyrrole-1-carboxylate (2.00 g, 6.3 mmol) was dissolved in 1,4 -dioxane (35 mL) and degassed potassium acetate (1.86 g, 18.9 mmol), Pd(dppf)Cl2-CH2Cl2 (154 mg, 0.19 mmol), dppf (105 mg, 0.19 mmol), and bis(pinacolato)ethylborane (1.92 g, 7.56 mmol) were added sequentially to this solution under nitrogen protection . The reaction mixture was stirred and reacted at 80 °C overnight. Upon completion of the reaction, the crude reaction mixture was concentrated and purified by fast column chromatography on silica gel (15-50% EtOAc/hexane gradient elution) to afford tert-butyl 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,5-dihydro-pyrrole-1-carboxylate as a white semi-solid (1.50 g, 81% yield).1H NMR (CDCl3, 300 MHz) δ 1.26 (s, 12H), 1.46 (s, 9H), 4.18 (m, 4H), 6.45 (bd, 1H, J = 14.10 Hz); MS (ESI) m/z = 240.2 (MH+ -t-Bu).

References

[1] Patent: US2010/204265, 2010, A1. Location in patent: Page/Page column 91; 92
[2] Patent: TW2016/4185, 2016, A. Location in patent: Paragraph 0142; 0143
[3] Patent: WO2010/5783, 2010, A1. Location in patent: Page/Page column 152
[4] Patent: WO2016/65236, 2016, A1. Location in patent: Page/Page column 125
[5] Patent: WO2015/48662, 2015, A2. Location in patent: Page/Page column 58-59

1-Boc-2,5-Dihydro-1H-pyrrole-3-boronic acid, pinacol ester(212127-83-8)Related Product Information

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